Enjoy The Journey

Issue January/February 2022 February 2022 By Taylor Callahan
Young Lawyers Division Section Review
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Taylor Callahan

When I was in the first grade, I had the daunting assignment of writing my first book, a thrilling tale of a trip to my grandparents’ house a few miles down the road. More than 20 years later, the book has not surprisingly failed to become a bestseller, but the “About the Author” section still stands out clearly in my mind. The last sentence reads: “When I grow up, I would like to be a lawyer.” 

I like to think I was pretty advanced in predicting my career goals, but the reality is it didn’t quite take a crystal ball to see what inspired me. My parents are attorneys, as was my grandfather, who was also a commercial law professor at Suffolk Law for many years. Add in the fact many of my aunts and uncles are attorneys, and, well, you can clearly see where I got the idea. However, the road to my own legal career didn’t follow what I once considered the “traditional” path, and every time I missed a step in that journey, I thought I had failed. But now I’ve realized the only failure was in my thinking. 

I wish I had learned earlier — from someone outside my parents — that it’s okay not to follow the conventional path. Just because you aren’t taking the same steps as someone else doesn’t make you any less of an attorney. In fact, it can assist in bringing out the best qualities from within. 

Throughout college and my postgraduate years, I constructed in my head what I thought was the only path to becoming the best lawyer. Step one: Choose a legal-oriented college major. Step two: Get into a top-10 law school “day” program and graduate cum laude. Step three: Get a summer associate position each summer in big law. And step four: Get a job offer and work at said big law firm. While this is a fabulous and well-respected route, I think there is often a misconception in the legal field that only this trajectory produces the best attorney. Even among law students, those invited to participate in on-campus interviews are often rumored to be the best and brightest in the class. Each time I didn’t hit one of the aforementioned milestones or decided to take a different turn, the “failures” kept stacking up in my head. But I soon learned that what I gained by not choosing this so-called “traditional” attorney path has helped me in more ways than I could ever imagine. 

I graduated from Fairfield University with a double major in communication and music and a minor in Spanish — my first self-attributed “fail” in my path to be a lawyer. I then spent a year working as an administrative assistant as I pondered law school and studied for the LSATs. Working full-time and the other responsibilities of adulthood made it harder to go to law school through a day program, so I ultimately settled upon the evening J.D./MBA program at Suffolk University — a fantastic program but not what I had planned for myself. Cue my second “fail” in the unorthodox lawyer trajectory. I also knew that while continuing to work, I wouldn’t be able to pursue a summer associate job, where most law students can get their foot in at a prestigious firm. That meant I probably wouldn’t start my career at a big law firm — a “double fail” in my mind. Truthfully, I wasn’t even sure if I wanted to work in big law or in-house, but I thought starting at a more prominent law firm (or even at a law firm, in general) was the only and best way I could start my career.

My misconceptions couldn’t have been further from the truth. While I was so-called “failing,” I was actually growing in my career in more ways than one. I gained further interest in the investment management and securities regulation legal field at the investment consulting firm I worked at. I eventually became an investment contract specialist in our OCIO/Discretionary department, where I worked closely with our legal team and gained a vast amount of knowledge. At the same time, I earned a role as a research assistant to one of my professors at Suffolk Law, assisting him with various tasks for a textbook he was co-developing, which furthered my passion in the investment management regulation field. I passed the ever-so-daunting bar exam and joined the Massachusetts bar in November 2018. 

I continued my work on our OCIO team but still wondered, was this what I was supposed to be doing? Did I make the right choice? Then, finally, this summer, it clicked. I was presented the opportunity to join our legal team as assistant counsel and realized at that moment every step I had taken before was the right one. Whenever I thought I had “failed,” I was really failing to realize, everything I had done was a step in the right direction. It led me to exactly what I ultimately had always wanted — an in-house counsel position. 

I would not be where I am today had I not followed the path meant for me. You always hear, “it’s not just the result, but how you got there that counts,” and, as cliché as it sounds, it’s true. It’s hard to remember that in the moment, and I wish following a nontraditional path was highlighted to law students beyond just “J.D. Alternative” job postings or that all law schools offered evening programs. It’s okay not to be invited to “on-campus interviews”; it’s okay that you don’t have a summer associate position. In the end, you’ll be proud of your journey and how it shaped the person you’ve become. 

All of this is to say: You don’t always need to race to the finish line. Instead, enjoy the journey you are on. Too often, we worry about what we aren’t doing or if we are doing enough or as much as someone else. This is your reminder that you are exactly where you need to be. 

Taylor Callahan works as assistant counsel at NEPC LLC in Boston. She currently serves on the Board of the Massachusetts Bar Association’s Young Lawyers Division, where she is co-chair of the Community Service Committee. In her free time, she enjoys spending time with her family and friends, traveling (outside of a global pandemic), being “auntie” to her nephew and six nieces, spending time by the ocean, being active, and creating and listening to music.